IL37406A - 3-alkoxy-and 3-alkylthio-2,6-dinitroaniline compounds and their use as herbicides - Google Patents
3-alkoxy-and 3-alkylthio-2,6-dinitroaniline compounds and their use as herbicidesInfo
- Publication number
- IL37406A IL37406A IL37406A IL3740671A IL37406A IL 37406 A IL37406 A IL 37406A IL 37406 A IL37406 A IL 37406A IL 3740671 A IL3740671 A IL 3740671A IL 37406 A IL37406 A IL 37406A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- carbon atoms
- alkyl
- accordance
- halo
- Prior art date
Links
- 239000004009 herbicide Substances 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 claims abstract 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract 8
- 230000002363 herbicidal effect Effects 0.000 claims abstract 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 241000196324 Embryophyta Species 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000004094 surface-active agent Substances 0.000 claims 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 claims 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 239000005864 Sulphur Chemical group 0.000 claims 1
- 150000004703 alkoxides Chemical class 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- -1 dinitro aniline Chemical compound 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 231100000208 phytotoxic Toxicity 0.000 claims 1
- 230000000885 phytotoxic effect Effects 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000000969 carrier Substances 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
- A01N33/18—Nitro compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
N-Substituted 2,6-dinitro-3-alkoxyanilines having a halo, lower alkyl, or trifluoromethyl substituent at the 4-position. The compounds are useful as pre- or post-emergence herbicides and can be formulated with the usual herbicide carriers.
[US3764624A]
Claims (15)
1. Compounds of the general formula in which is an alkyl group of at least 2 carbon atoms or an alkenyl, alkynyl, cycloalkyl, cyoloalkenyl or phenyl .group and R2 if? hydrogen or an alkyl, alkenyl, alkynyl, cycloalkyl or cyoloalkenyl group (any of which groups ¾_ and R2 may be halo-i hydroxy- or lower alkoxy-subs ituted) or R^ and Rg. together represent a chain including 2-6 carbon atoms which with the nitrogen atom forms a saturated heterocyclic group, is. lower alkyl, Y is oxygen or sulphur and Z is lower alkyl, halo or trifluoromethyl.
2. · A compound in accordance with claim 1 in which is alkyl of 2 to 6 carbon atoms, Rg is hydrogen or alkyl of 1 to 6 carbon atoms, is alkyl of 1 to 3 carbon atoms and Y is oxygen, the total number of carbon atoms represented by + Eg being about A to 8·
3. · A compound in accordance with claim 2 in which Z is trifluoromethyl.
4. ·· A compound in accordance with claim in which Z is chloro,
5. · A compound in accordance with claim 2 i which Z is methyl,
6. · N-sec-butyl-2,6-dinitro-3~methoxy-- trifluoromothylaniline·
7. · N,N-<5&-n-propyl-2,6-di^ trifluoromothylonil.i mi·
8. &-3-e 1^l<-^6~<-li itro~3^ methylaniline.
9. Any of the herbicidal compounds hereinbefore identified.
10. A method of preparing a compound according to claim 1, which comprises reacting in substantially equimolar amounts an alkali metal .alkoxide or an alkali metal thioalkoxide and the 5-halo-2,&dinitro aniline corresponding to the desired compound.
11. A herbicidal composition comprising a compound according to any of claims 1-9 or as prepared by the method of claim 10, and a carrier therefor,
12. A composition according to claim 11 in which the carrier is a liquid diluent or a solvent together with a surface active agent.
13. 15. A composition according to claim 11 in which the carrier is a pulverulent solid optionally with a surface active agent,
14. The method for controlling weed growth which comprises applying to the locus of said weeds a phytotoxic amount of a compound as defined in any of claims , 1-9 or as prepared by the method of claim 10.
15. The method in accordance with claim 14, in which about 0.1 to 30 pounds of said compound are applied
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6142870A | 1970-08-05 | 1970-08-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL37406A0 IL37406A0 (en) | 1971-10-20 |
| IL37406A true IL37406A (en) | 1976-02-29 |
Family
ID=22035710
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL37406A IL37406A (en) | 1970-08-05 | 1971-07-28 | 3-alkoxy-and 3-alkylthio-2,6-dinitroaniline compounds and their use as herbicides |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US3764624A (en) |
| AT (1) | AT311315B (en) |
| AU (1) | AU459328B2 (en) |
| BE (1) | BE770936A (en) |
| BR (1) | BR7104999D0 (en) |
| CA (1) | CA943957A (en) |
| CH (1) | CH565739A5 (en) |
| DD (1) | DD96136A5 (en) |
| DE (1) | DE2135140B2 (en) |
| ES (1) | ES393862A1 (en) |
| FR (1) | FR2101862A5 (en) |
| GB (1) | GB1308841A (en) |
| IL (1) | IL37406A (en) |
| IT (1) | IT941655B (en) |
| NL (1) | NL150659B (en) |
| OA (1) | OA03772A (en) |
| PL (1) | PL83205B1 (en) |
| SU (1) | SU370753A3 (en) |
| ZA (1) | ZA715199B (en) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4227913A (en) * | 1971-06-30 | 1980-10-14 | American Cyanamid Company | Inhibiting plant bud growth with substituted 2,6-dinitroanilines |
| US3920742A (en) * | 1971-08-25 | 1975-11-18 | American Cyanamid Co | N-sec-alkyl-2,6-dinitro-3,4-xylidine herbicides |
| US4251264A (en) * | 1971-08-25 | 1981-02-17 | American Cyanamid Company | 2,6-Dinitroaniline herbicides |
| US4165231A (en) * | 1971-08-25 | 1979-08-21 | American Cyanamid Company | 2,6-Dinitroaniline herbicides |
| US4066441A (en) * | 1971-08-25 | 1978-01-03 | American Cyanamid Company | Preemergence herbicidal methods and compositions using 2,6-dinitroxylidine compounds |
| US4166908A (en) * | 1971-08-25 | 1979-09-04 | American Cyanamid Company | 2,6-Dinitroaniline herbicides |
| US4057419A (en) * | 1972-02-29 | 1977-11-08 | Bayer Aktiengesellschaft | 2,4-Bis-(trifluoromethyl)-6-nitrophenol compounds and herbicidal compositions |
| US4123250A (en) * | 1972-04-19 | 1978-10-31 | American Cyanamid Company | Inhibiting plant bud growth with substituted 2,6-di-nitroanilines |
| US3950377A (en) * | 1972-12-20 | 1976-04-13 | Imperial Chemical Industries Limited | Diphenylamine derivatives |
| US4041172A (en) * | 1972-12-20 | 1977-08-09 | Imperial Chemical Industries Limited | Compositions and methods for combating insect pests or fungal pests of plants |
| US4046758A (en) * | 1974-03-05 | 1977-09-06 | United States Borax & Chemical Corporation | 3-Halo-2,6-dinitro-4-trifluoromethylanilines |
| US4192670A (en) * | 1974-10-15 | 1980-03-11 | Eli Lilly And Company | Acetal derivatives of 4-(substituted amino)-3,5-dinitrobenzaldehydes |
| CA1106390A (en) * | 1974-12-04 | 1981-08-04 | Don L. Hunter | Nitrophenylhydrazine compounds |
| US3958974A (en) * | 1974-12-20 | 1976-05-25 | Velsicol Chemical Corporation | Herbicidal N-aryl substituted azetidinones |
| US3979453A (en) * | 1975-06-23 | 1976-09-07 | Eli Lilly And Company | 3-Cyanamino-2,6-dinitroanilines |
| US4180568A (en) * | 1975-06-23 | 1979-12-25 | Eli Lilly And Company | Control of phytopathogens with certain 2,6-dinitroanilines |
| US4101582A (en) * | 1975-12-22 | 1978-07-18 | American Cyanamid Company | 2,6-Dinitroaniline herbicides |
| US4124639A (en) * | 1975-12-22 | 1978-11-07 | America Cyanamid Company | N-alkoxyalkyl-2,6-dinitroaniline herbicides |
| US4045466A (en) * | 1976-03-19 | 1977-08-30 | Eli Lilly And Company | 3-Cyanoalkylthio- or 3-alkoxycarbonylmethylthio-2,6-di-nitroanilines |
| US4133672A (en) * | 1977-02-07 | 1979-01-09 | United States Borax & Chemical Corporation | (Aminophenyl)morpholines and use thereof |
| US4297127A (en) * | 1977-03-11 | 1981-10-27 | American Cyanamid Company | Herbicidal use of 2,6-dinitroaniline herbicides |
| US4152460A (en) * | 1978-01-30 | 1979-05-01 | Eli Lilly And Company | 3-Chloro-2,6-dinitro-N-(substituted phenyl)-4-(trifluoromethyl)benzenamines |
| US4259347A (en) * | 1978-02-16 | 1981-03-31 | Eli Lilly And Company | Control of phytopathogens using dinitroaniline compounds |
| US4391992A (en) * | 1979-08-24 | 1983-07-05 | American Cyanamid Company | N-Denitration of N,2,6-trinitroanilines with phase transfer catalysts |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE571267A (en) * | 1957-09-17 | |||
| BE628133A (en) * | 1962-02-08 | |||
| US3257190A (en) * | 1962-12-10 | 1966-06-21 | Lilly Co Eli | Method of eliminating weed grasses and broadleaf weeds |
| US3403180A (en) * | 1963-10-07 | 1968-09-24 | Lilly Co Eli | 4-trifluoromethyl-2, 6-dinitroanilines |
| US3518076A (en) * | 1967-05-17 | 1970-06-30 | Lilly Co Eli | Method of fliminating weed species with herbicidal combination |
| US3546295A (en) * | 1968-08-01 | 1970-12-08 | Exxon Research Engineering Co | N-cycloalkyl anilines |
-
1970
- 1970-08-05 US US00061428A patent/US3764624A/en not_active Expired - Lifetime
-
1971
- 1971-06-10 CA CA115,378A patent/CA943957A/en not_active Expired
- 1971-07-14 DE DE2135140A patent/DE2135140B2/en not_active Withdrawn
- 1971-07-20 FR FR7126470A patent/FR2101862A5/fr not_active Expired
- 1971-07-22 GB GB3488971A patent/GB1308841A/en not_active Expired
- 1971-07-26 AT AT646271A patent/AT311315B/en not_active IP Right Cessation
- 1971-07-28 IL IL37406A patent/IL37406A/en unknown
- 1971-07-28 CH CH1114071A patent/CH565739A5/xx not_active IP Right Cessation
- 1971-08-03 PL PL1971149810A patent/PL83205B1/pl unknown
- 1971-08-03 ES ES393862A patent/ES393862A1/en not_active Expired
- 1971-08-03 DD DD161898A patent/DD96136A5/xx unknown
- 1971-08-04 BR BR4999/71A patent/BR7104999D0/en unknown
- 1971-08-04 AU AU32014/71A patent/AU459328B2/en not_active Expired
- 1971-08-04 IT IT27180/71A patent/IT941655B/en active
- 1971-08-04 ZA ZA715199A patent/ZA715199B/en unknown
- 1971-08-04 BE BE770936A patent/BE770936A/en unknown
- 1971-08-05 SU SU1689351A patent/SU370753A3/ru active
- 1971-08-05 OA OA54323A patent/OA03772A/en unknown
- 1971-08-05 NL NL717110826A patent/NL150659B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US3764624A (en) | 1973-10-09 |
| OA03772A (en) | 1971-12-24 |
| AU459328B2 (en) | 1975-03-20 |
| IT941655B (en) | 1973-03-10 |
| NL150659B (en) | 1976-09-15 |
| CA943957A (en) | 1974-03-19 |
| GB1308841A (en) | 1973-03-07 |
| DE2135140B2 (en) | 1980-06-19 |
| AU3201471A (en) | 1973-02-08 |
| AT311315B (en) | 1973-11-12 |
| ZA715199B (en) | 1972-04-26 |
| NL7110826A (en) | 1972-02-08 |
| PL83205B1 (en) | 1975-12-31 |
| BE770936A (en) | 1971-12-16 |
| BR7104999D0 (en) | 1973-02-15 |
| IL37406A0 (en) | 1971-10-20 |
| DD96136A5 (en) | 1973-03-12 |
| SU370753A3 (en) | 1973-02-15 |
| DE2135140A1 (en) | 1972-02-10 |
| ES393862A1 (en) | 1974-07-16 |
| CH565739A5 (en) | 1975-08-29 |
| FR2101862A5 (en) | 1972-03-31 |
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